Catalytic ring opening of α-epoxyketones using DDQ in methanol solution at room temperature and under reflux conditions in excellent yields

Abstract

Catalytic ring opening reactions of α-epoxyketones by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in methanol solution at r. t. and under reflux conditions resulted in the formation of α-hydroxy-β- methoxyketones through Cβ-O bond cleavage in excellent yields. Whereas the type and nature of the additional substituent affects the rate of ring opening, the effect of temperature has an extreme influence on the rate of reactions. Cyclic voltammetric studies of DDQ at 15°C and 33°C support the increased electron-acceptor ability of DDQ by the increasing of temperature. © 2007 Verlag der Zeitschrift für Naturforschung.